UIC

The First Address in Short Path Distillation

Production of
High Concentrated Monoglyceride
by Willi Fischer
Lecture given on occasion of the
DGF-Symposium in Magdeburg / Germany
in October 1998

Production of High Concentrated Monoglyceride

Willi Fischer, UIC GmbH, Alzenau Hrstein

Main consumer of Monoglyceride is the food industry and quantities required are so
high, that worldwide several companies have specialized on Monoglyceride as their
main production. Monoesters with C16/C18 acid groups are preferred. If a high amount of
unsaturated acids is present, e.g. if the iodine value is >80 the final product is a liquid or
a jelly at room temperature. If the iodine value is <2, Monoester have melting points of
about 70C. Products with 40 60 % Mono content can be achieved direct by the synthesis. High concentration requires an additional distillation. Pic. 1 shows an overview
of the major process steps.

Starting
Material
Fat or
Fatty Acids,
Glycerine,
Chemicals

Synthesis

Crude Low
Concentrated
Monoglyceride

Distillation

Glycerine free
Low Concentrated
Monoglyceride

High
Concentrated
Monoglyceride

Monoglyceride Production Process

Overview

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Finishing

Liquid

Powder;
Chips;
Flakes

Pic.1
Monovort.xls

Starting from Acids, the chemical reaction is a direct Esterification, while starting from
Triglycerides, Interesterification is involved as shown in Pic. 2.

Direct Esterification (Fatty acid plus Glycerine)

Main Reaction
1 RCO2H
Acid

+ 1 C3H8O3
Glycerine

1 RCO2C3H7O2

1 H2O

Monoglyceride

Water

Secondary Reaction
1 RCO2C3H7O2
Monoglyceride

+ 1 RCO2H
Acid

1 (RCO2)2C3H6O +

1 H2O

Diglyceride

Water

Interesterification (Fat or Oil plus Glycerine)

Main Reaction
1 (RCO2)3C3H5
Triglyceride

+ 1 C3H8O3
Glycerine

1 RCO2C3H7O2

1 (RCO2)2C3H6O

Monoglyceride

Diglyceride

Secondary Reaction
1 (RCO2)2C3H6O + 1 C3H8O3
Diglyceride

Glycerine

2 RCO2C3H7O2
Monoglyceride

Reaction Formulas for Synthesis of Monoglyceride

Pic.2
Monovort.xls

Secondary reaction of direct Esterification reduces the concentration of Monoglycerides

but cannot be avoided as it happens simultaneously.

Both types of synthesis lead to an equilibrium which is as more on the right side as
higher the temperature and as longer the reaction time is. To maintain a high quality in
the final product, the temperature is limited to approx. 240C and the residence time on
this temperature should not exceed half an hour. The concentration at the end of the reaction is 40 60 %. It should be noticed, that water is created by direct Esterification.
To avoid uncontrolled foaming by too sudden water formation, the reaction speed must
be dampened while for Interesterification there is not such a limitation.

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The dominating part of the manufacturing cost is the price for the feed material. Acids
and Glycerin are more expensive than Triglycerides. Also only 0.67 mole of Glycerin is
required for one mole of Monoglyceride by Interesterification while direct Esterification
requires one mole of Glycerin for one mole of Monoglyceride. Therefore manufacturing
costs for direct Esterification are higher and this method is done only if Monoglycerides
with a specified Acid distribution is required. Interesterification produces Monoglycerides
with the same Acid distribution as in the Triglyceride. Limited change is only possible by
blending of different Triglycerides and hydrogenation of the double bounds. Pic. 3
shows, that basically always Fat or Oil, is the feed material for both type of reaction.

Fat, Oil

Splitting

Glycerine

Fatty Acids
Esterification

Interesterification

Monoglyceride

Transformation of Fat or Oil into Monoglyceride

Pic.3
Monovort.xls

The reaction speed is forced by employment of a catalyst. In production plants soaps of

elements of the first and second row of the periodic system are used. Sodium and Potassium soap can be removed easier after reaction, while Calcium soap shows a slightly
higher activity.

To push the equilibrium towards Monoglyceride by excess Glycerin, 73 wt% of fat and
27 wt% of Glycerin are recommended to add to a batch. The excess Glycerin is not
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complete soluble in the Fat and intensive mixing is required. Pic. 4 shows an overview
of product streams including recycling.
Batch operation

Continuous operation

11
3

1
Reactor
1

Reactor
2

Recycle
Tank

Decanter

Stripper

Distillator

LoMo
Tank

10

12

Reaction step (kg/batch)

Stream Name
Stream no.

Fat

Glycerine Recycle 1

Total Quantity

Mix 1

Mix 2

Glycerine Low Mono

6

--

--

3.770

7.615

7.618

510

7.108

2.773

--

--

--

--

--

--

Glycerine

--

1.072

587

1.094

1.094

485

609

Monoglyceride

--

--

449

3.561

3.561

15

3.546

Diglyceride

--

--

2.566

2.774

2.774

--

2.774

Others

--

--

168

168

169

10

179

Fat

Distillation step (kg/h)

Stream Name

Low Mono Strip. Dist. Strip. Bott. Recycle 2 High Mono

Stream no.

Feed/h

2.706

324

2.382

1.132

1.250

272

264

Monoglyceride

1.328

30

1.289

138

1.160

Diglyceride

1.039

--

1.039

961

78

67

30

37

33

Glycerine

Others

10

11

12

Product Streams of Mono-Process

(Interesterification of hydrogenated Tallow)

Pic.4
Monovort.xls

After reaction, 15 % of unreacted Glycerin is still left in the mixture. Only 6 - 7 % of Glycerin is soluble in the Glyceride phase. 8 - 9 % Glycerin can be separated by settling.

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The Glyceride phase contains about 50 % Monoglyceride, 7 % free Glycerin, 40 % Diglyceride and 3 % of a mixture of Triglyceride, Diglycerine, free Acids and traces of
catalyst or decomposed catalyst.
For some applications the separated Glyceride phase can be sold direct. For other application the so called Low Mono with less than 1 % of Glycerin is required. The Glycerin is stripped either in a flash column or better in a wiped film evaporator at some
mbar. Very often a concentration of >90 % Monoglyceride with low content of free Acids
and Diglycerine and free of Ash is required. For the production of this so called High
Mono the distillation of Low Mono is necessary. This can be done only by Short Path
Distillation at approx. 200C and 0.01 mbar or less.

Pic. 5 shows the sectional view of a distillation unit for a feed rate of 13 000 mt/a Low
Mono. The quantity of High Mono recovered from the Low Mono can vary from 40 55
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% of the total content depending on what concentration is required. Monoglyceride is

the distillate, Di- and Triglyceride remain in the residue.
In the Monoglyceride molecule the acid group is coupled with Glycerin either in - or in
position. The -Mono content is wanted as high as possible as it has a much higher
emulsifying effect as -Mono. Just after reaction, the -Mono portion can be 7 % of total. During storage some -Mono will be converted into -Mono and the content can be
as low as 2 % if conversion is completed. Therefore the specification of -Mono content
is not precise and is depending on the time when the sample is analyzed. In elder literature we find often the specification of -Mono while in our time total Mono content is
specified. Reason is, that the wet analysis which was used in former time can determine
only -Mono while the GC method now used measures the total Mono content.

The residue from the Mono concentrating is recycled to the reaction process and is further converted into Monoglyceride. Approximately 50 % of the recycled residue is converted into Monoglyceride at each recycle. After 6 recycles, about 98 % of the fat is converted finally into Monoglyceride. As for each reaction batch fresh Fat and fresh Glycerin is added the averaged residence time of the material in the process is between 2
and 3 passes. As longer the residence time of the material in the process as more
thermal degradation can happen. The acceptable number of recycles is determined by
the quality specs. of the final product and is influenced by the quality of the feed material, but more by adequate equipment, precise operating conditions and proper storage.
E.g. nitrogen blanketing of material at elevated temperature shall be considered. Manufacturers told as that recycle rates ranging from 3 to more than 25 recycles are usual.
Unlimited number of recycle is only theoretically a 100 % use of material. A small
amount of Glycerides is purged with the settled Glycerin after reaction. From the material balance of an existing plant over an extended time of operation and with more than
20 recycles, the lost of fat was calculated in the range of 2-3 %.

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High excess quantity of Glycerin in the feed mixture is required for several reasons. It
was already mentioned, that excess Glycerin pushes the equilibrium to the right side of
the reaction formula. As the catalyst is promoting also the reaction backwards there is a
risk, that Monoglyceride is disproportioned during Glycerin stripping Therefore it is necessary to deactivate the catalyst. The deactivation is done by adding Phosphoric Acid.
The Phosphate will be extracted from the mixture by the insoluble portion of Glycerin. It
is removed from the process together with the settled Glycerin. To avoid recycling of the
Phosphate in the process, the settled Glycerin must be distilled before it can be recycled to the reactor.

An alternative which does not require a redistillation of the settled Glycerin each time is
the use of Calcium soap as a catalyst. Calciumphosphate is insoluble in Glycerin and
can be separated by filtration or with a centrifuge. However this is somewhat difficult
and there is a risk, that the ash content is higher in the final product. Also it has to be
considered that Diglycerine together with undistilled Glycerin is recycled and will increase the content in the final High Mono.

On production scale, direct Esterification as well as Interesterification can be done continuously or batchwise. As today more than 90 % of Monoglyceride is produced by Interesterification only this route shall be further discussed.

For continuous reaction one equipment configuration can be a mixing vessel followed
by a pipe reactor.

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Reflux
condenser

Reflux
condenser

Steam ejectors

Deactivating
chemicals

Catalyst

Cooling
water

Reactor 1

Steam

Reactor 2

Cooling
water

Scrubber

Decanter

Cooling
water

Liquid
ring
pump
Cooling
water

Steam

To hotwell

Fat,
Glycerine,
Recyclemixture
Precipitated
Glycerine

Glyceride
mixture

Batch Reactor System for Monoglyceride Synthesis

Equipment Diagram

Pic.6
Monovort.xls

A simplified equipment diagram of a 3 stage batch reactor system is shown in Pic. 6.

Reactor 1 is a steam heated mixing vessel with a reflux condenser. In this vessel the
mixture is heated till the required concentration of Monoglyceride is reached. Then the
mixture is pumped into the second reactor and cooled as fast as possible, to minimize
reverse reaction. After catalyst deactivating the and settling is finished, Glycerin and
Glyceride mixture are pumped to separate storage tanks.

The total batch time is almost 9 hrs. However, in a 3 vessel reactor system as shown
the vessels are operated in an overlapping mode which allows to finish all 3,5 hrs an
other batch and nearly 7 batches can be made in 24 hrs. The batch volume has to be
considered carefully. Too small reactors cause higher specific manufacturing and operating cost. Too large reactors designed with a small l/d ratio are expensive again and
very powerful, high energy consuming agitators are required. If l/d is high, the much
heavier Glycerin phase is not carried quickly enough in the upper section and emulsion
equilibrium is not reached.

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Experience taught us, that reactors for a batch volume of 5 - 10 m are somewhat an
optimum. The design of the reactor system must also consider GMP rules and especially low thermal degradation. Heating with steam rather than with hot oil reduces temperature overshooting. Recommended material of construction is Inox according to
German code 1.4571 or American code 316.

Condenser
Steam ejectors
Cooling
water

Stripped
Glycerine

Glycerine
stripper

Rectfication
tower

Steam

Monoglyceride
distillator

Oil
booster
pump

Scrubber

Hot
oil

Liquid
ring
pump

Cooling

Hot
oil

Cooling
water

To hotwell

Cold trap
Glyceride
Mixture
after
Reaction

High Monoglyceride
Quench cooler

Cooling
water

Low Monoglyceride

Diglyceride

Continuous Distillation System for High and Low Monoglyceride

Equipment Diagram

Pic.7
Monovort.xls

Pic. 7 shows the simplified equipment diagram of a double stage distillation plant for
Monoglyceride. In the first stage Glycerin is stripped in a thin film evaporator with rectification tower and an external condenser. Glycerin free Low Mono can be discharged via
a quench cooler from this step. For High Mono production, the bottom product is
pumped into the following Short Path distillator with internal condenser, where
Monoglyceride is concentrated in the distillate.

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10

Both evaporators are thin film evaporators indirect heated with thermal oil. Vacuum is
produced by an oil booster pump followed by a multiple stage steam ejector system and
a liquid ring pump. Driving fluid for the oil booster pump and the liquid ring pump is
Glycerin. This will avoid contamination with a non food grade auxiliary medium in case
of operating or plant failure.

Thin Film Evaporator Series RF

Short Path Distillator Series KD

Pic. 8 shows the principle of thin film evaporators with and without internal condenser.
For economical reasons high availability of the distillation is essential. Modern plants
are operated with net distillation time of 8000 hrs/a. This is an uninterrupted operation
24 hours a day for 7 days a week all year round. Only one shut down per year for maintenance is necessary. To maintain the high quality specs for the final product, fouling on
the evaporator surface must be avoided. Experienced manufacturers of agitated film
evaporators deliver equipment with fine polished surface and optimal roller wiper system to fulfill these requirements.

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11

The economical figures, especially the production of high concentrated Monoglyceride

which requires a higher investment shall be analyzed. Pic. 9 shows the annual key data
of 1994 of a production plant with a capacity of 10 000 mt/a.

Input
Unit price
Hardened Soy Oil
Glycerine

Quantity

Annual cost
US$

930

US$/mt

8.319

mt/a

7.736.670

48,8

2.050

US$/mt

1.815

mt/a

3.720.750

23,5

105.000

0,7

1.400.000

8,8

Rework of settled Glycerine

Share of plant cost per year

Portion
%

1)

Steam 40 barg

61

US$/mt

8.900

mt/a

542.900

3,4

Steam 12 barg

56

US$/mt

2.400

mt/a

134.400

0,8

305 US$/MWh

750

mt/a

228.750

1,4

880 MWh/a

72.160

0,5

150.000

0,9

260.000

1,6

1.500.000

9,5

15.850.630

100,0

Fuel
Electricity

82

US$/mt

Other utilities, instrument air,

nitrogen, cooling water,
waste disposal, etc.
Labor cost

50

US$/h

Overheads
Total

2)

Output
Unit price

Quantity

Annual gross
profit
US$

High concentrated Mono

1)

2.140

US$/mt

9.840

mt

21.057.600

Total Plant Investment is 7.000.000 US$. 20% of this sum covers depreciation, intrest rate,
insurance, etc. per year.

2)

Cost do not include packing, transport and distribution and sales activity.

Cost/Profit Break Out of Figures of 1994

Plant Capacity: 10.000 mt/a High Mono

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Pic.9
Monovort.xls

12

This plant makes good profit even if the additional distribution costs are considered. Interesting is a look on the cost increments. Feed material is almost 72 % of the total cost,
while 9% is overheads. Only the remaining 19 % of the cost can be influenced by engineering and production management. Energy, maintenance, labor are small portions
and must not be analyzed furthermore. The remaining portion for plant investment with
less than 9 % is reasonable.

However as the investment is high, purchase departments tend to decide more on price
rather than on technical performance to save money. However this is not smart at all.
Due to strong competition amongst bidders for this type of plants the range for high and
low price bids are max. 10 %, which is only 1 % cost saving. If less investment would
reduce the yield by only 2 % this would increase the feed material cost portion by about
1.5 %. This shows the relation. The same is true for reduced maintenance efforts.

Another aspect is the minimum size where profit is made at all. As some cost factors
are constant, others linear and some reverse proportional, there is a minimum production where break even is reached. This is dependent on market situation, infrastructure,
environmental regulations, annual load etc.

To support the decision of potential investors, our company has developed an in-house
calculating program for quick calculation of economical key data. Pic. 10 shows several
cases of investigation of different sizes often requested in an early stage of investment
decision. It is astonishing, how much break even can differ depending on the
conditions.

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13

P ro d uc tio n c a p a c ity o f hig h

c o nc e ntra te d M o no g ly c e rid e

P ro d uc tio n c o s t re la tiv e to g ro s s
s a le s p ric e

m t/a

C ase 1
1 .3 0 0
5 .0 0 0
1 5 .0 0 0
1 .8 5 0

107
87
79
(B re a k e v e n)

1 .3 0 0
5 .0 0 0
1 5 .0 0 0
1 .2 3 0

98
81
70
(B re a k e v e n)

1 .3 0 0
5 .0 0 0
1 5 .0 0 0
3 .5 0 0

117
95
86
(B re a k e v e n)

1 .3 0 0
5 .0 0 0
1 5 .0 0 0
2 .0 3 0

108
87
74
(B re a k e v e n)

C ase 2

C ase 3

C ase 4

Case
N e t. p ro d uc tio n tim e /y e a r
S o urc e fo r ra w m a te ria l
F a b ric a tio n p ro g ra m

Infra s truc ture

E nv iro nm e ta l re g ula tio ns
R e a c tio n p ro c e s s
N o . o f R e c y c le s

2
7 .5 0 0

O uts id e
M o no g ly c e rid e
o nly
M e d ium le v e l
H ig h
B a tc hw is e
>6

3
8 .0 0 0

Inho us e
O the r O le o c he m ic a ls a s
w e ll
H ig h le v e l
H ig h
B a tc hw is e
>6

4
6 .4 0 0

O uts id e
O the r O le o c he m ic a ls a s
w e ll
M e d ium le v e l
Low
B a tc hw is e
>6

8 .0 0 0
O uts id e
M o no g ly c e rid e
o nly
H ig h le v e l
H ig h
C o ntinuo us
>6

In flu en ce o f P la n t S ize o n P ro d u ctio n C o st

C o m p a riso n o f d iffe re n t S c e n a rio s

P ic .1 0
M on ovort.xls

Summarized we can say, that the technology for the production of Monoglyceride has
reached a high level so far. Under the pressure of global competition plant manufacturers as well as producers are forced to optimize the technology further. Based on todays
experience remarkable improvement of the distillation technique is not expected. However improvement of the synthesis and optimized operating conditions seem to have
room for further improvement in the near future. It will be interesting to see the results.

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14